121216-42-0

Basic information

• Product Name: (S)-2-Amino-1,2,3,4-tetrahydro-7-methoxynaphthalene
• Synonyms: (S)-7-METHOXY-1,2,3,4-TETRAHYDRO-NAPHTHALEN-2-YLAMINE;(S)-(-)-7-METHOXY 2-AMINOTETRALIN;(S)-7-METHOXY-2-AMINOTETRALIN;(S)-2-AMINO-1,2,3,4-TETRAHYDRO-7-METHOXYNAPHTHALENE;(S)-2-Amino-7-methoxy-1,2,3,4-tetrahydronaphthalene;(S)-2-AMINO-7-METHOXYTETRAHYDRONAPHTHALENE HCL;2-NaphthalenaMine, 1,2,3,4-tetrahydro-7-Methoxy-, (2S)-;(S)-2-(N-benaylaMine)-7-Methoxytetralin
• CAS NO: 121216-42-0
• Molecular Formula: C11H15NO
• Molecular Weight: 177.24
• Mol File: 121216-42-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 203 °C
• Boiling Point: 299.6°Cat760mmHg
• Flash Point: 139.7°C
• Appearance: /
• Density: 1.056g/cm³
• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.547
• PKA: 10.21±0.20(Predicted)
• CAS DataBase Reference: (S)-2-Amino-1,2,3,4-tetrahydro-7-methoxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Amino-1,2,3,4-tetrahydro-7-methoxynaphthalene(121216-42-0)
• EPA Substance Registry System: (S)-2-Amino-1,2,3,4-tetrahydro-7-methoxynaphthalene(121216-42-0)

Safety Data

• Hazardous Substances Data: 121216-42-0(Hazardous Substances Data)

Usage

Uses

(S)-7-Methoxy-2-aminotetralin is an intermediate in many organic synthesis such as the synthesis of potent and orally bioavailable tetrahydronaphthalene raf inhibitors and the synthesis of Sodium Oxo-De(aminodimethyl) Bedoradrine-13C, d2 (S634552), a labeled selective β-adrenergic stimulant.

InChI:InChI=1/C11H15NO/c1-13-11-5-3-8-2-4-10(12)6-9(8)7-11/h3,5,7,10H,2,4,6,12H2,1H3/t10-/m0/s1

Upstream product

• 83343-23-1 N-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine 
• 3880-78-2 7-Methoxy-1,2,3,4-tetrahydro-(2R)-2-naphthaleneamine hydrochloride 
• 121251-88-5 (S)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (S)-mandelate 
• 4133-34-0 7-methoxyl-2-tetralone 
• 231623-76-0 N-[(2S)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]benzamide 
• 4003-89-8 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene 
• 231623-74-8 N-(7-methoxy-3,4-dihydro-naphthalen-2-yl)-benzamide 

Downstream Products

• 1274817-11-6 N-[(2S)-7-((2-[(cyclopropylcarbonyl)amino]pyridin-4-yl)oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-3-[(dimethylamino)methyl]-5-(trifluoromethyl)benzamide hydrochloride 
• 194785-79-0 (7S)-7-amino-5,6,7,8-tetrahydronaphthalen-2-ol hydrobromide 
• 121524-14-9 ((S)-7-{tert-Butoxycarbonyl-[(R)-2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-acetic acid ethyl ester 
• 121489-30-3 [(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethyl]-((S)-7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester 
• 121489-29-0 tert-butyl [(2R)-2-(3-chlorophenyl)-2-hydroxyethyl][(2S)-7-hydroxy-1,2,3,4-tetrahydro-2-naphthalenyl]carbamate 
• 121251-86-3 (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(S)-3-chloromandelamide 
• 121251-84-1 (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(R)-3-chloromandelamide 
• 121216-34-0 (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(S)-mandelamide 
• 121216-33-9 (-)-N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(R)-mandelamide 
• 742664-85-3 N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(2S)-2-(3-chlorphenyl)-2-hydroxyethanamine 
• 121216-31-7 N-<(2S)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl>-(2R)-2-(3-chlorphenyl)-2-hydroxyethanamine 
• 85951-60-6 (-)-7-OH-AT 

Relevant articles and documents

Asymmetric amination of tetralone and chromanone derivatives employing ω-transaminases

Various (S)-selective and (R)-selective ω-transaminases were investigated for the amination of 1- and 2-tetralone and derivatives as well as of 3- and 4-chromanone. All ketones tested were aminated to give the corresponding enantiopure amines (ee > 99%) employing at least one of the enzymes investigated. In most of the cases the (S)- as well as the (R)-enantiomer was obtained in optically pure form. The amination of 3-chromanone was performed on a 100 mg scale leading to optically pure (R)-3-aminochromane (ee > 99%) with complete conversion and 78% isolated yield.

Asymmetric hydrogenation of trisubstituted N-acetyl enamides derived from 2-tetralones using ruthenium-SYNPHOS catalysts: A practical synthetic approach to the preparation of β3-adrenergic agonist SR58611A

The asymmetric hydrogenation of various trisubstituted enamides derived from 2-tetralones under mild reaction conditions using Ru-SYNPHOS catalysts is reported. This practical and clean method gives access to several chiral 2-aminotetralins derivatives in high isolated yields and enantiomeric excesses up to 95% depending on the substitution pattern of the aromatic ring and the nature of the amide moiety. In addition, the usefulness of the current method is demonstrated via a practical synthetic approach to the enantiomerically pure SR58611A compound, a potent and selective β3-adrenergic receptor agonist.

Alternative synthesis of the chiral atypical β-adrenergic phenylethanolaminotetraline agonist SR58611A using enantioselective hydrogenation

We have developed an alternative synthesis of the atypical β-adrenergic phenylethanolaminotetraline agonist SR58611A. Two key intermediates have been synthesised involving enantioselective hydrogenation of an aminoketone and an enamide providing the corre